


Dude (Looks Like A Lady)

by loves_music17



Category: Drake & Josh
Genre: Anal Sex, Crossdressing, Language, Lingerie, M/M, Semi-Public Sex, Step-Sibling Incest
Language: English
Status: Completed
Published: 2016-01-10
Updated: 2016-01-10
Packaged: 2018-05-12 23:00:36
Rating: Not Rated
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,940
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/5684461
Author URL: https://archiveofourown.org/users/loves_music17/pseuds/loves_music17
Summary: <blockquote class="userstuff">
              <p>Josh helps Drake embrace his feminine side.</p>
            </blockquote>





	Dude (Looks Like A Lady)

Drake has always been on the feminine side, Josh thought to himself as he sat in the kitchen eating a sandwich. His petite frame, fair complexion, and skintight clothing make him appear more fragile and vulnerable, like a woman, to Josh anyway. Not that Josh was the manliest guy around either, but since he’d started working out and lost all of his baby fat there was a noticeable difference between the two of them now. Josh loves the fact that he can pick Drake up with ease, manhandle the other boy, and there’s nothing Drake can do about it. Not that Drake minds Josh showing off his superior strength. No matter how much he denies it, Josh knows Drake secretly gets off on it as much as he does.

\-- 

Upstairs, Drake is lying on his bed playing his guitar thinking much the same thing as his step-brother. The two teenagers have been secretly dating for close to six months now. With all of the not so platonic kisses and hugs they’ve shared over the years, it was really only a matter of time before they took things further. They started out with hushed fumbling handjobs in the dark of their bedroom but quickly moved on to giving each other blowjobs in the 69 position that resulted in the best orgasms either boy had ever experienced. Of course they have rough patches just like any other couple and argue only slightly less than they did when they weren’t dating, but the one thing they are good at is reading each other. And sex, the sex was phenomenal. Josh wasn’t just amazing in the sack; he was like a tiger that had been released from its cage. All that strength and physical power was focused entirely on Drake and it left the smaller boy aching in the most pleasurable of ways for days afterwards. The mere thought of it made him harden in his too tight skinny jeans.

\--

They were both strictly speaking virgins before they got together, contrary to what Drake would have others believe. When they finally decided to stop trying to repress their true feelings for one another and see if a relationship would work between them, Josh insisted they have a serious heart-to-heart conversation about their limits. Not surprisingly for the two teenage boys, there were very few, being as adventurous as they are. When Drake said he didn’t see the point in them wearing condoms since they weren’t girls and couldn’t get pregnant, Josh made it clear that, that meant Drake could no longer date girls then. Josh wants a completely monogamous relationship and didn’t want to worry about Drake contracting something. It was hard for Drake to get used to the idea of no longer being able to flirt with or date girls. He’d hid behind the player persona for so long, in denial of his desire to be with his step-brother. Not to mention others took notice in Drake’s sudden disappearance from the dating scene and subsequent increase in time spent with Josh. Eventually though, people stopped paying attention and it wasn’t like it was so abnormal for the two teens to spend more time together. They’d become known for being attached at the hip after all. They were Drake and Josh, singular. When their friends or family saw them separated the first question was always where the other one was or what they were up to but no one had any idea that they might be closer than typical brothers. There were a couple close calls where they’ve almost been caught in compromising positions though. Josh couldn’t help but grin at the memories despite how terrified they’d both been at those times. To be honest, Josh had a hard time keeping his hands off Drake, who was so naturally sexy and had no clue the effect he had on Josh with his brief touches between classes or how his obsession with nibbling on the end of his pen drove Josh crazy. Everything Drake does practically screams “fuck me” and Josh is more than happy to comply. Come to think of it, he’s probably upstairs right now, caressing his guitar the same loving way he caresses Josh’s dick, the little minx. Josh surreptitiously adjusts his pants beneath the table before rising to go upstairs, sandwich completely forgotten.

\--

It would have been impossible not to hear the larger boy’s thundering footsteps as Josh makes his way up to Drake’s and his room. Drake quickly climbs down from his lofted bed, wanting to tuck his beloved instrument away before Josh comes in and starts tossing him around like the ragdoll he sometimes mistakes Drake for when they get carried away. He barely makes it to his guitar stand before Josh is in the room and crossing the few short feet between them to wrap his beefy hands around Drake’s slim waist and grinding his evident arousal into Drake’s ass.

Josh leans down to nuzzle Drake’s neck, breathing in the intoxicating scent that is so unique to the other boy, before he whispers huskily, “I was downstairs thinking about all the ways you tease me with your slutty little games and thought you might need a reminder of who you belong to. Am I right, Drake?” 

Josh moves one of his hands down to squeeze the prominent bulge in Drake’s pants, applying pressure until Drake has to rise up on his tiptoes to stave off the pain but at the same time moves his ass back towards Josh’s groin in open invitation. Drake clutches at Josh’s muscular forearm, not sure if he’s trying to get Josh to relieve some of the pressure or apply more. Josh ignores his touch though; he will do as he pleases with Drake regardless. Even when Drake is unsure what he wants or needs, Josh seems to have some instinctual knowledge and although he pushes Drake to his limits he never topples him over the edge unless he is sure Drake can handle it and will enjoy it. Drake loves that he can give up all of his control to Josh and how easily the other teen wields it. Despite Josh’s anxious attitude toward most things in life, he is clearly the dominant partner in their relationship.

Drake is brought back to the present when Josh applies that extra bit of pressure that makes Drake gasp and whimper as Josh says, “I believe I asked you a question, Drake. It’s clear though that you do need a reminder if you can so easily ignore me.”

Before Drake has time to process what’s happening Josh hefts him up over his shoulder fireman style and Drake has the brief sensation of falling as he is flung onto Josh’s bed. The action leaves him breathless and his hair mussed, much to his chagrin—Josh taught him that word a couple weeks ago and Drake hopes he used it correctly. In the next instant Josh is tugging him back to the edge of the mattress by his ankle, wasting no time in unbuttoning and unzipping Drake’s jeans. Neither of them can help but chuckle a bit at the excessive wriggling and tugging it takes to get the smaller boy out of said jeans. Every time they do this Josh complains about Drake’s obsession with girl pants and Drake smugly replies that if it’s so much of a hassle he can stop wearing them which is usually enough to shut Josh up about the matter. 

Today though, when Drake counters with this argument Josh looks up at him with a positively wicked gleam in his eyes and says, “Or maybe I’ll just dress you up like a real girl since you seem to like it so much.”

Drake’s stomach flutters strangely at the thought, and Josh has to have noticed the way his cock twitches in interest. But the other boy doesn’t say anything, acts like he didn’t catch Drake’s reaction to his words, and continues to strip Drake until he’s completely naked and laid out for him like a feast. Drake watches eagerly as Josh efficiently removes his own clothing in record time, his eyes devouring every inch of Josh’s muscular body. Once Josh starts ravishing him it doesn’t take long for Drake to forget about the incident altogether as he’s consumed with Josh’s passionate lovemaking.

\--Three weeks later…

“Josh, that is the last time I let you rope me into helping you with one of your science experiments. Look at me! I’m covered in- in- I don’t even know what this is but it’s yucky and slimy and I hate it!” Drake rants as he follows Josh down the hall to the gym locker rooms.

Josh gives Drake a look over his shoulder that effectively cuts off any other possible comments Drake might have made as Josh replies, “You know, best I recall you were the one who asked to help. All I wanted you to do was sit there patiently while I did a practice run for the science fair next week. But nooo, you wanted to feel useful. So I asked you to stir some of the compounds for me and of course you couldn’t do that without causing a chemical reaction that resulted in your current ‘yucky, slimy,’ state. I don’t see how this is my fault at all, really, unless you count me thinking it was okay to let you help in the first place.”

Drake huffs and juts out his delicious lips in a pout that has no right being as cute as it is but makes no further arguments as the pair trudge towards the locker rooms where Josh plans to take Drake’s clothes to wash them. It was almost seven o’clock on a Friday night so the school was thankfully empty and Josh was suddenly struck by a very appealing idea that has been festering in the back of his mind for weeks now. At the last second he veers off the path towards the guys’ locker room and instead heads in the direction of the girls’. Thankfully, Drake being the trusting, naïve, and admittedly not so bright boy he is doesn’t even question the change in direction. It could be that he just has no clue where the guys’ and girls’ locker rooms are, seeing as he hasn’t attended a single gym class in his entire life and regularly forges excuses to skip the class. All the better for what Josh has in mind though.

Within a minute Josh is pushing open the door to the girls’ locker room and ushering Drake in after him. Drake unselfconsciously starts shedding his drenched and smelly clothes right in front of Josh, who has no plans on objecting to the show. Josh does chance a quick glance around the room just to make sure his plan will work and when he finds what he was searching for he can hardly contain his delight. Once Drake is naked he turns to look at Josh as he wipes at the viscous fluid on his skin with his nose adorably wrinkled in disgust. Josh quickly scoops up Drake’s clothes and chirpily instructs Drake to take a shower while he goes to wash them in the laundry room down the hall before ducking back out the door. Not that he needs to tell Drake that, the boy was halfway to the shower room before the door had fully swung shut. Josh can’t help but snicker as he walks away from the locker room. He wonders how long it will take Drake to realize Josh has no intention of bringing his clothes back.

For a boy notorious for his lack of patience, Drake waits a solid hour after getting out of the shower before he starts to doubt Josh’s return. Just to be sure he waits another thirty minutes, shivering slightly as he drip dries in the drafty locker room. His brownish red hair has curled cherubically without the aid of styling products or a straightener, softening his already androgynous features to the point that he could be mistaken simply for a girl with a short haircut. It suddenly dawns on Drake to try to call Josh to see what the holdup is but this hope is swiftly crushed when he realizes his cell phone was in the pocket of his jeans. In the next instant he is struck by another thought; he’s in the locker room where the guys change for practice so maybe some of the guys left something in the lockers he could wear temporarily just to track down Josh. He goes to investigate the lockers and finds that all of them have locks on the metal doors, unfortunately. Drake’s shoulders slump dejectedly before his eyes spot one lone locker without a lock. He rushes over to open it and is horrified at what he finds. 

Josh tricked him, he thinks bitterly. This isn’t the guys’ locker room, it’s the girls’! Inside the unlocked locker innocently lays a pair of the shortest shorts Drake has ever seen and a shirt that somehow manages to look big and yet at the same time Drake knows will be too short even for him who is the same height as most of the girls in their high school. Upon closer inspection Drake recognizes the outfit as Raechel’s, a pretty girl in his and Josh’s English class who wore it the day before at school. She must have changed for cheerleading practice and forgot to take the clothes with her as well as lock her locker. Drake hesitantly picks up the shorts first, his heart feeling like it’s about to burst out of his chest. What if someone walks in and sees him? As he shifts the pants to his other hand a pair of lacy black panties falls out of the shorts before fluttering to the floor in slow motion, or at least it feels like it to him. Drake gulps audibly. There’s no way he’s putting those on. Looking at the shorts though it is blatantly obvious if he tries to wear them without the underwear his junk will just spill out of the leg, and how mortifying would that be? He mentally curses females and their ridiculously skimpy clothing, even though he used to live for every peek of flesh he could glimpse from a girl. 

Before he can talk himself out of the decision he slips on the panties, berating himself for liking the way the lace feels against his bare skin. After he settles the underwear on his bony hips he notices for the first time that a hole has been intentionally made in the back, right over his asshole as if…Raechel you dirty girl. Drake laughs out loud as he looks over his shoulder at his reflection in the mirror, admiring the way the material hugs his ass and imagining Josh pounding into him while Drake wears the lacy panties. No longer so squeamish about the prospect of putting on the rest of the outfit, actually a little eager to see the completed look to be honest, Drake tugs the shorts up his legs. For the first time in his life Drake is glad he isn’t a hairy guy and his legs are mostly smooth because otherwise it would just look freaky for him to be wearing booty shorts so short that the pockets hang lower than the hemline. There is lace on the pants as well where the bottom sides have been cut and replaced with white lace, and the denim is intentionally distressed to show off small patches of Drake’s thighs. Drake was right about needing to wear the panties too; the shorts barely cover the swell of his ass and he finds his dick swelling in the lace as well as straining against its denim confines at an alarming rate. His face flushes red as he picks up the black tee shirt, a midriff top he recalls the girls calling them, with a picture of The Beatles on the front—at least Raechel has good taste in music— that falls to just above his navel and slides provocatively off one shoulder. Now that Drake is actually wearing the clothes, he discovers that mysterious fluttering feeling has returned to his stomach which he is currently idly stroking as he gazes fully at himself in the mirror. Josh wants to see him in girls’ clothes, huh? Well, it can’t be said that Drake doesn’t dive in headfirst whenever a challenge is given to him. 

He turns back to the locker with purpose, surveying the contents left inside. There’s a makeup bag perched on the shelf and he snags it before turning back to the mirror. He’s put on his fair share of stage makeup for shows with his band, but only enough to make his face pop for the crowd. He deftly applies the eyeliner, foundation, lip-gloss, and blush though before moving on the mascara. It’s harder than it looks he realizes after nearly jabbing his eye out but in the end he figures it out. There’s a container of black nail polish as well and Drake painstakingly paints all of his finger- and toenails with the tiny brush. All in all it takes him a good twenty minutes to do this but he is inconceivably proud of his work and just knows Josh won’t be able to control himself once he gets a look at him in this getup. The finishing touch is putting on the shoes, a pair of black ankle-length heels made to look like boots a 1960’s punk might wear that lace up in the front and have silver buckle straps on the sides. Drake takes the time to practice walking, not wanting to fall and break an ankle and then have to explain what he was doing in heels in the first place at the ER.

Slowly but steadily he cautiously exits the locker room, peering around the corner to make sure no one is around to see him. The coast is clear so Drake hesitantly heads toward the laundry room where he hopes Josh is waiting, because it is obvious now he meant for Drake to find the girl’s clothes and come find him. Sure enough, when Drake pokes his head into the laundry room he sees Josh leaning against the wall of washers with a smirk like a cat that ate the canary. Drake fully enters the room with a sigh, but before he can take two steps Josh holds up an authoritative hand in the universal gesture for stop.

“I could hear you coming a mile away in those shoes, even over the machine. You look dead sexy by the way. Why don’t you give us a twirl to show off your outfit, I’m sure you’ve already practiced knowing you, you little girl,” Josh says teasingly.

Drake ducks his head to hide the blush Josh’s words cause, because he did in fact practice twirling before he left the locker room. Josh clears his throat meaningfully after a moment and Drake hurries to comply with his order. He does three quick successive twirls before Josh orders him to go more slowly so he can properly enjoy the view. After Josh is satisfied he motions for Drake to come over towards him which Drake does, albeit a bit tipsily from all of the spinning. As he reaches Josh he gracelessly trips right into the other boy’s arms but once he’s there he has no intention of leaving the embrace and instead snuggles into Josh’s burly chest. 

Josh allows him a few moments to get his bearings before he bodily lifts Drake off the ground and takes two steps to plant the lithe teen on top of the dryer which is vibrating as it dries Drake’s clothes. Drake can feel the machine’s vibrations throughout his entire body and it feels deliriously good. Josh watches him knowingly, his lips still quirked with a little smirk. He tenderly brushes aside a curly lock of Drake’s hair that was obscuring his face before leaning down to plant an equally tender kiss on the tip of Drake’s button-nose. Drake’s eyes cross for a second as he tries to squint down at the spot Josh kissed. Then he feels Josh place a possessive hand on his thigh, thumb stroking circles over his inner thigh until Drake obligingly spreads his legs for easier access.

“Oh, you’re so easy aren’t you, baby?” Josh murmurs before he places another chaste kiss against Drake’s prominent collarbone.

Drake moans breathily, unknowingly playing right into his feminine role, as he lets his head loll to the side in invitation for Josh to mark him, to make Drake his. Josh does so gladly, biting and sucking at Drake’s pale neck until there is a deep, dark bruise in the shape of his mouth for the whole world to see. Drake moves his legs to tightly wrap them around Josh’s waist at the same time Josh moves to pull Drake’s shorts down. The shorts only make it to Drake’s knees before Josh plunges his hand into the front of the lace panties, stroking Drake’s cock tortuously slowly as Drake whines for more.

“You’re all wet down here, Drake, just like a girl. We already knew you were a slut though, didn’t we? You’re my slut though, right?”

Drake can’t contain his mewl of desire, “Yeah, Josh, all yours, only yours. Please, Josh, please fuck me, now.”

Josh tsks disapprovingly, “But I’ve only just got to look at you. I want to savor this. I’ve waited two hours for you to figure out what you were supposed to do tonight so I think you can wait a little longer you eager thing.”

Any complaint Drake may have voiced is swallowed when Josh claims his mouth in a bruising kiss that lasts until they both are forced to come up for air and leaves Drake’s lips deliciously plump and red. Throughout the kiss, Josh continues to pump Drake’s shaft, running his thumb over the slit that leaks copious amounts of precome but always backing off as Drake reaches the verge of climax. His own dick feels hard enough to pound nails at this point and he deftly undoes his belt and shimmies out of them to alleviate some of the pain. Drake has dissolved into a writhing mass of need between Josh’s ministrations and the dryer’s incessant vibrations. He’s nearly in tears by the time Josh takes mercy on him and holds up two fingers for Drake to suck. Drake does so eagerly, laves them like they were Josh’s actual dick, coating them in saliva so that when Josh pulls them away with a wet pop there is a trail of spit between the digits and his mouth that is obscenely hot to see. 

At Josh’s prompting he scoots his bottom to the edge of the machine so that Josh has easy access to his exposed hole. Josh pushes in both slick fingers effortlessly up to the second knuckles, and Drake relishes the momentary burn as Josh stretches him. Drake can’t help himself from grinding back on Josh’s scissoring fingers, wantonly trying to fuck himself on the digits. When Josh removes his fingers Drake thrashes wildly for a moment as Josh wipes up Drake’s precome, which has formed a decent sized puddle on his stomach, to use as slick for his cock. Josh hushes Drake gently as he presses him down by his hips to keep him from moving as he lines up his dick with Drake’s quivering hole. Only once Josh has entered Drake does the other boy calm down marginally though his chest still heaves raggedly. Josh reminds Drake to bear down as he pushes in, to smooth the process. It still fascinates Josh to watch Drake’s body swallow up his cock until he is balls deep and his hips are flush with Drake’s ass. Today there is the added bonus of feeling the layer of lace between them. 

When Josh is fully seated inside Drake, he gradually pulls back out until only the tip of his penis is still wrapped in the velvety walls of Drake’s passage. Then he thrusts back in just as gently, though it is torture for them both to not just drive into his body like a jackhammer, but he doesn’t wish to cause his lover any harm. After a couple minutes of this Josh feels Drake is ready for more and increases his pace accordingly, pounding into Drake’s unresisting form while he clutches the boy’s hips so hard there will undoubtedly be bruises there later. Drake doesn’t mind, if his ceaseless litany of pleas for harder and faster are anything to judge by. Then they both reach the point where words fail them and the silence is only broken by the sound of skin on skin and occasional grunts and moans. Drake’s nails scour Josh’s back in his lustful fever but Josh hardly feels the scratches as he continues to batter Drake’s hole with a single-minded purpose.

Then Drake is crying out, “Oh, oh, God, Josh! I’m c-I...” and his seed gushes out onto his bare stomach as his channel clenches like a vise around Josh’s dick until Josh releases inside Drake with a drawn out groan.

They collapse together on top off the dryer, panting heavily as they try to catch their breath. After a minute Drake moans miserably as he says, “Josh, the…the machine, please, turn it off. I can’t- it’s too much.”

Josh blinks blearily down at Drake, not understanding what the boy means until he notices the dryer is still going at full speed and Drake is probably very sensitive after they each had such earth-shattering orgasms. He slams his fist into the ‘STOP’ button, making Drake sigh in relief. They continue to lay there for an unknown amount of time, but by the time they move to separate they’ve become glued together with Drake’s dried come. After carefully extricating himself Josh pulls up his pants and shuffles over to get a wet paper towel from the sink in the corner of the room. When he returns he tenderly wipes off the come on Drake’s stomach as well as his own seed which is starting to drip between Drake’s thighs. He doesn’t think he’ll ever tire of the sight of his come dripping out of Drake’s just-fucked ass.

“Next time, I think I’ll bring a plug so I can keep my come in you for later and you’ll be even less likely to forget who you belong to,” Josh proclaims as he chucks the dirty towel in the general direction of the trash bin.

Drake smiles as Josh helps him to his feet, “I take it you want to do this again, then?”

“Planning on it, actually,” Josh says, “I’d keep you like this 24/7 if I could, trust me. I’ve never come so hard in my life.”

Josh watches in amusement as Drake works to right his borrowed clothes even though his own clothes are in the dryer right behind him, “Planning on walking out of here with that on, babe?”

Drake looks up with wide eyes, mouth open in surprise at his own actions. Josh crowds the smaller boy back against the machine, one hand sneaking under the hem of his shirt to play with his nipples while the other grips Drake’s ass firmly.

“Not that I’m complaining mind you. You’re hot as hell in this, but don’t you think Raechel will miss her clothes?”

Drake shrugs innocently, “I’d feel bad putting them back after what we did with them, wouldn’t you? Besides, I think she’d have a hard time figuring out who took them."

Josh grins, “That is a valid point. But you should probably still change before we leave, just in case someone happens to see us.” 

Drake leans up to peck Josh on the lips before he begins to shimmy out of the clothes. When he takes his own clothes out of the dryer he finds himself reluctant to put them back on. He hesitates for a brief second before donning his old outfit, though he instantly dislikes the heaviness of his male clothes and feels much less sexy all of a sudden. He doesn’t understand, because he’s never thought of himself as the type of guy who is into crossdressing but after tonight he has to reconsider his feelings. He knows he would never be brave enough to dress like a girl in public but he realizes he likes the forbidden element to wearing girls’ clothes in private.

As Josh takes his hand and they make their way toward the front entrance of the school after stuffing Drake’s stolen outfit in a plastic bag, the larger boy leans down to whisper conspiratorially in Drake’s ear, “I don’t see any reason why you wouldn’t be able to wear those sexy lace panties underneath your regular clothes, even at school. No one but us would be any the wiser after all. I could order you some more too, you know.”

Drake can’t contain his grin at the idea, “Really? Could I help pick them out?”

Josh nods magnanimously while laughing, “Of course. What do you think about a red thong with a little bow in the back for Christmas? Then you’d be like a perfect little present wrapped up just for me to open.”

Drake agrees eagerly and they spend the entire drive home thinking up things to order online for Drake to wear. Good thing Josh gets paid soon, because Drake is ready to embrace his feminine side.

The End


End file.
